A low temperature transfer hydrogenation of N=N, C=O or C=C bond using rhodium bipyridine catalysts

Inorganic Chemistry Communications

Volumn 8, Issue 1, 2005, Pages 94-95

  Frediani, Piero ^a   Salvini, Antonella ^a   Bessi, Martino ^a   Rosi, Luca ^a   Giannelli, Carlo ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Alkenes; Azo compounds; Bipyridines; Hydrogen transfer; Ketones; Rhodium

Indexed keywords

PYRIDINE; RHODIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COVALENT BOND; HYDROGENATION; LOW TEMPERATURE; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 10944254996     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2004.11.013     Document Type: Article

References (18)

1. G. Mestroni, G. Zassinovich, and A. Camus J. Mol. Catal. 2 1977 63 64
2. G. Mestroni, G. Zassinovich, and A. Camus J. Organomet. Chem. 140 1977 63 72
3. C. Fragale, M. Gargano, and M. Rossi J. Mol. Catal. 5 1979 65 73
4. C. Botteghi, G. Chelucci, G. Chessa, G. Delogu, S. Gladiali, and S. Soccolini J. Organomet. Chem. 304 1986 217 225
5. G. Mestroni, G. Zassinovich, E. Alessio, and M. Tornatore J. Mol. Catal. 49 1989 175 185
6. S. Gladiali, L. Pinna, G. Delogu, S. De Martin, G. Zassinovich, and G. Mestroni Tetrahedron Asymmetry 1 1990 621 634 and references therein cited
7. J.E. Backvall J. Organomet. Chem. 652 2002 105 111
8. Y. Himeda, N. Onozawa-Kumatsuzaki, H. Sugihara, H. Arakawa, and K. Kasuga J. Mol. Catal. 195 2003 95 100
9. H-U. Blaser, C. Malan, B. Pugin, F. Splinder, H. Steiner, and M. Studer Adv. Synth. Catal. 345 2003 103 151
10. P. Selvam, S.U. Sonovane, S.K. Mohapatra, and R.V. Jayaram Adv. Synth. Catal. 346 2004 542 544
11. P.M. Gidney, R.D. Gillard, and B.T. Heaton J. Chem. Soc., Dalton 1972 2621
12. 2O (3) were synthesised following the procedure reported for the other complexes [11]. Elemental analysis: found % (calcd.) C 41.67 (41.48), H 3.76 (3.77), N 7.90 (8.06). IR and multinuclear NMR are in agreement with those of the above reported complexes
13. The catalytic reactions were carried out in glass vial inserted in a 150 mL stainless steel autoclave rocked in a thermostated bath (±1°C). A solution of propan-2-ol (10 mL), NaOH (125 μmol), Rh complex (0.674 mM) and substrate (59.0 mM) was prepared in a Schlenk tube and transferred into the vessel. At the end of the reaction, the solution was collected and analysed by GC or HPLC. GC-MS spectra were collected to confirm the nature of the products obtained
14. The pre-activated catalysts were prepared by heating a propan-2-ol solution (10 mL) of the complex (0.674 mM) in the presence of NaOH (125 μmol) at 80°C for 4 h, then cooled to room temperature. The substrate was added (59.0 mM) and the transfer reactions were performed at the prefixed temperature for 3 h. The solution was analyzed as above reported
15. A.J. Blacker, B.J. Mellor, (Zeneca Ltd., UK) PCT Int. Appl., 1998, 36 pp, WO 9842643 A1 19981001
16. K. Murata, T. Ikariya, and R. Noyori J. Org. Chem. 64 1999 2186 2187
17. Q.G. Mazzulani, S. Emmi, M.Z. Hoffman, and M. Venturi J. Am. Chem. Soc. 103 1981 3362 3370
18. S.G. Yan, B.S. Brunschwig, C. Creutz, E. Fujita, and N. Sutin J. Am. Chem. Soc. 120 1998 10553 10554